γ-CF<sub>3</sub>-Allenamides versus 3-CF<sub>3</sub>-Cyclopentenylamines: Substituent-Controlled Divergent Reaction of β-CF<sub>3</sub>-1,3-Enynamides with β-Dicarbonyl Compounds
A distinctive <i>N</i>-substituent-controlled regioselective 1,4-hydrocarbonation or 1,4-hydrocarbonation/5-<i>endo</i>-<i>trig</i> cyclization cascade reaction of β-CF<sub>3</sub>-1,3-enynamides with β-dicarbonyl compounds in the presence of a simple base is reported. β-CF<sub>3</sub>-1,3-enynamides having a Ts group <i>N</i>-substituent produce γ-CF<sub>3</sub>-allenamides via a 1,4-hydrocarbonation process, whereas β-CF<sub>3</sub>-1,3-enynamides bearing a Ms group <i>N</i>-substituent lead to 3-CF<sub>3</sub>-cyclopentenylamines through a 1,4-hydrocarbonation/5-<i>endo</i>-<i>trig</i> cyclization cascade process.
Authors
- Yuanjing Xiao (ORCID: https://orcid.org/0000-0002-0185-1961)
- Jintong Li
- Lei Wang (ORCID: https://orcid.org/0000-0002-8792-0234)
- Mingqing Liu (ORCID: https://orcid.org/0000-0002-2465-4143)
- Yulin Wu (ORCID: https://orcid.org/0000-0003-4027-8173)
Institutions
- East China Normal University (CN)
- Yangzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-09-10
- DOI
- https://doi.org/10.1021/acs.joc.4c01669
- Citations
- 5
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.04
Funders
- National Natural Science Foundation of China
- Science and Technology Commission of Shanghai Municipality